Schooner Woodwind Sailing Cruises

We celebrated our anniversary with the Schooner Woodwind Sunset Beer Tasting Cruise and it was absolutely incredible! Captain Jen and her crew were fantastic—so welcoming, knowledgeable, and fun. The weather was perfect, and Captain Jen took us out by the iconic Thomas Point Lighthouse while sharing stories and history about it and other local landmarks. The highlight for me was getting the chance to actually drive the schooner! Sailing on such a beautiful boat has always been a dream of mine, and being able to take the helm made it truly unforgettable. The craft beers, the sunset views, and the atmosphere all added to a perfect evening. This was hands down one of the best experiences we’ve ever had together. If you’re looking for something unique and memorable, the Schooner Woodwind is it!

Absolutely fantastic experience! The boat was beautiful, the wind was perfect, the crew was fantastic, and the team was completely accommodating. As somebody who gets seasickness very easily, I was pleased that the way the boat moved didn’t trigger a single feeling of nausea. It was really fun. Looking forward to doing it again soon.

After several sails with Captain Jen and crew, it keeps getting better and better! This is an amazing way to spend a few hours on the bay whether a special day or just because! Wonderful experience from beginning to end, every time! Def recommend!!! Looking forward to the next time we can sail :)

My family came together in Annapolis for my Dad’s 80th birthday and he requested a sail. I found Schooner Woodwind through a google search and we couldn’t have had a better time. They made his day truly special. We booked a group in advance which allowed us to ensure we had a spot on the boat and they rolled out the red carpet for us. They had a special sign for us wishing him a happy birthday. We were able to board first and sit as a group (16 of us) in the stern. Captain Jen even let us take turns at the helm. We had great conditions that day and really enjoyed our sail all the way out to the lighthouse and back. Thanks for an amazing, memorable day. We hope to return sometime soon

Had an amazing trip and the crew was great! The captain assured all passengers were safe, but also enjoyed their voyage through the bay! I did the sunset beer tasting cruise with my wife, and it was an awesome experience. I would definitely recommend this as part of your trip to Annapolis!

We had an amazing experience on our sunset sailing cruise. It is a great way to see downtown Annapolis from the water. It was a slow cruise with beverages served. The crew was great and even allowed a few passengers to steer the sailboat. We would do this again in a heartbeat!

Friendly, knowledgeable crew who made the sail fun! We had a perfect afternoon out on the water and got to help the crew raise the sails. I would HIGHLY recommend this activity for anyone looking for a fun and relaxing activity to do in Annapolis. Captain Delaney and crew were awesome.

Captain Jennifer and her entire crew made this experience unforgettable! We joined for Wednesday Race night so there were hundreds of boats in the water, really cool to see. A must if you like to sail and are in the MDV area.

A friend and I sailed on Saturday and I've already recommended this outing to all of my colleagues and local DC friends! Captain Jen and her crew were great--from welcoming everyone aboard, to the safety briefing, to answering a million questions, to serving drinks--they were knowledgable and fun. Joey and Jake were great crew, too. It was the perfect day to be on the water as it was SO HOT but windy and clear for sailing. Will definitely bring my family next time!

Nice relaxing sunset sail. 2 hours fly by with a tour of the bay and interesting facts about the area and its history.

Always smooth sailing on the Woodwind Schooner. Easy to purchase tickets, great communication about what expect, all details are included! Very knowledgeable and happy staff, you can expect to learn a lot about sailing and the area's points of interest!

what fun! a must- do if you're visiting Annapolis. Trips are 2 hours, see some cool sights, and you can take the helm (or hoist a sail) if you'd like. The crew and Captain were SO accommodating.

If you need a different idea for date day look no further than the schooner woodwind. 2-hour sales out on the Chesapeake Bay out of downtown Annapolis with all the comforts of boat ownership without any of the headaches. Well worth every penny, especially if the weather is nice The cruise super nice and they serve drinks on board both alcoholic and not. It's a fair price for what you get and the capstone for any day date in Annapolis. Highly recommended as we have been three or four times now and look forward to it annually. The owner and her staff could not be more friendly.

The ship is awesome ! The ride was beautiful! Very very friendly and accommodating staff and crew that made our experience wonderful!

I'm writing this review to help future guests be aware and to share a recent disappointing experience I had regarding your ticketing process. Back in August, I purchased two tickets for the Sunset Sail. Unfortunately, the second guest was unable to attend. I arrived at the dock two hours early to explain the situation to Joe. I didn't request a refund--knowing the tickets were non-refundable--but asked if the unused ticket could be honored on a standby basis for a future sail. Joe agreed and advised me to call a few days in advance when I was ready to rebook. Three weeks later, my parents were interested in experiencing the Sunset Sail after hearing how much I enjoyed it. I called Joe to redeem the standby ticket and to purchase an additional ticket for the second person. Before making the purchase, I asked specifically if both guests would be able to board. Joe assured me they would. However, on the day of the sail, my parents arrived early (around 4:45 PM), only to be told by Joe that only one confirmed ticket existed, and the second guest would have to wait to see if someone didn't show up. By 5:20 PM, I received a message from my mother saying they would not be able to board because they had a standby ticket. I immediately called Joe for clarification. Instead of acknowledging the confusion or taking accountability, he referred me to the standby policy and offered vague excuses. As a consolation, he mentioned the both tickets could now be used on any future date--but unfortunately, the moment was already lost. Why would I have knowingly purchased only one ticket if I had been told in advance that the second person might not be able to board--especially for what I understand is your most popular sail? This experience not only wasted my parents' time but also reflected poorly on your customer service approach. While the boat, crew, and scenery were truly fantastic during my own visit, this experience has left me disappointed. It's not about the money--it's about trust, communication, and how guests are treated. I hope you take this feedback seriously and use it to improve how such situations are handled in the future.

We had a fantastic time on the Schooner. This is a sailboat so you will be exposed to conditions like the sun, etc. The weather for our sunset ride was perfect. We were seated next to the captain who was very nice and knowledgeable. However, this isn't a boat ride where the captain gives history or points out landmarks, etc. It's a ride, not a tour. I would love to go back for a specialty cruise-they have beer cruises, history ones, etc that sound like fun.

Went on a two hour 11am tour Sunday Memorial weekend, booked a week in advance. I was a little concerned about getting the reservation in time since the bookings open a week in advance, but I was able to get two tickets with several openings remaining within an hour after reservations opened. The four person crew was communicative during the sailing portions, asking for volunteers to help raise and lower the sails, and chatty/friendly while we sailed around the harbor. There were 20-25 other people on the boat with several children, and I appreciated that the crew especially engaged with them (letting them steer the ship). We motored in and out of the dock, but otherwise sailed for the majority of the time on the boat. Ticket came with a free drink. It was my first time on a sailboat, and I enjoyed the chitchat with the staff and the tour the captain gave of the sights. Great experience - worth the $60+ ticket for an Annapolis summer morning! Remember to wear sunscreen. (They also offer life jackets for those interested.)

This is wonderful sailing experience. A definite must do while visiting Annapolis. The crew, boat and tour were all exceptional.

A 21 year tradition continues! .... each year on or near our wedding anniversary we take a cruise aboard the sailboat we were married on. Yesterday was our day to celebrate sharing life's journey together! The winds were blowing perfectly which lead to a fantastic afternoon sailing adventure! Looking forward to many more years of cruising with my beautiful bride aboard Schooner Woodwind: Annapolis Sailing Cruises ... Founded and operated by the Kaye Family since July 1993 ... The Schooner Woodwind is a first class business that provides outstanding service and an exceptional sailing experience. We might be slightly bias but if you are visiting Annapolis we wholeheartedly recommend Schooner Woodwind: Annapolis Sailing Cruises! Check them out on the web at: https://schoonerwoodwind.com/

Great crew, great boat, and great evening on the water! Who knew that our boat was the one they used in The Wedding Crashers?!!!

It's always a wonderful experience sailing with Schooner Woodwind and being able to watch the Blue Angels from the water was extra special! Captain Jen and the crew were engaging and kind.

Incredible sail with great owner Captain Jen. We are sailors and will sail for a week here but wanted some local knowledge so we signed up for the tour. We had all kinds of weather and had all 5 sails up. Customers get to help with the sails and steer should they want to. Jen gafe is lots of information on where to sail and places to eat for our week here. The boats are awesome and very impeccably maintained. I highly recommend the trip.

I booked 4 spots on this sail and the staff were lovely! They were full of fun facts and very accommodating with our schedule snafu. Thanks again for a great sail. We will be back!

Beautiful ship and great crew! Was a wonderful first time sailing experience will definitely want to do again! Highly recommend! They sail through November in October would be beautiful to see the autumn foliage from the sailboat!

While in town visiting friends, they surprised us with a sunset cruise. The breeze was perfect and the beers were ice cold. Our staff was funny and educational as they answered all sorts of questions from the other guests. Also had the pleasure of helping raise the sail which makes for a good story.

Brought my mom out on the Woodwind II for her birthday and it was absolutely wonderful. Cap'n Mickey & the crew were fantastic, very informative, & funny. It was incredibly peaceful. Looking forward to sailing again!

What an amazing experience!! Captain Jennifer and her Crew were very accommodating, friendly and true professionals. You're allowed to volunteer and join in on raising the sails or sit back and relax and take in the Chesapeake Bay. Highly Recommend It...A+++

A day spent on either Woodwind Schooner is always the best. But this Sunday it was a specialty music sail with Tony Lucca with perfect sailing weather with sun, blue skies and wind to make it even better. Captain Jen at the wheel and a great crew of Delaney, Michael & Jacob made it a perfect experience for all.

This was nice. Followed social distancing measures at line up and on boat. Thing is we thought we were buying a tour. Turn out this was just a sail ride and we made several circles lol. Very quiet should have some sort of music on board. Bought a bottle of champagne for $28 which was good. Can also tip crew online.

Such a beautiful schooner, and to see 2 of them sailing together! Many thanks to the great lady captain and her crew for a truly unique experience!

Sailing the Chesapeake Bay in a day with good weather is an amazing experience. The dock has plenty of parking. The crew does a great job setting the boat, and entertaining the their guest.

We had such an amazing time on our trip! Even though our trip was cut a little short due to lightning in the area, I felt like the captain had our best interest at heart by delaying our departure. I would highly recommend this experience to anybody. The staff on the boat is also amazing.

I scheduled this for my companies Executive Team and it was amazing. We sailed the 4:00 - 6:00 PM Private. The process of scheduling, ordering food, sailing was TOP NOTCH. Our Captain Jen and her crew took great care of us and made sure we had the perfect sail. I would highly recommend this from a personal sail to a team/company sail. KIM

Amazing time on the water. We were lucky to get great weather. Bring a sweater - once the sun starts going down it gets cold. We went during the week and there was no crowd. We could sit anywhere and were asked to help with the hoisting of the sails, totally fun! There were drinks and snacks... can't complain. Highly recommended.

This is an absolute must-do if you are in the Annapolis area! I booked an 11am tour on a Saturday a few days in advance, however, there were still tickets available for this cruise on the day of as I noticed some people purchasing them at the dock. The tickets said to arrive at 10:45am, and we were actually the first people there. It pays to be early because, as others have noted, they do really pack the boats so if you get there early, you have a better choice of seating. The weather was fantastic! The sun was shining, and we had a nice breeze for a while, so much so that we did not need all 4 sails raised until about half-way through our trip. Be mindful though that they sail rain or shine. The crew was entertaining, friendly, and efficient in getting drink orders to the passengers. They requested volunteers to help raise the sails, and if you wanted, you could hold the wheel and help the captain steer the ship. With your $44 ticket, you receive one complimentary soft drink/bottle of water plus a bagged snack (pretzels, chips, cookies, etc). If you check in on Yelp, you get a koozie that entitles you to one free beer each voyage you take with them. They do sell the koozie on the boat for non-Yelpers, but it is $3 and can only be used on the next voyage. Bryan W. and I both checked-in and received our koozies from the ticket window and were able to enjoy one free craft beer on the house. We were also first served once the sails were raised and they started to take drink orders. The beer selections were all local: Flying Dog, Port City, Heavy Seas, and Union Brewing. These were all $6 each (after our first free one of course) plus wine (pinot grigio and pinot noir) at $6, and champagne $25 only by the bottle. During our two hour cruise, the captain gave a narrative but due to the high winds, it was hard to hear most of the time. We sailed through Annapolis Harbor, past the Naval Academy, up the Severn River, and into the Chesapeake Bay. We saw the Thomas Point Lighthouse, Kent Island, and we almost made it under the Bay Bridge but due to the winds dying down, we had to turn around. We also saw an osprey with a fish in its mouth, and heard that the previous day, one of the cruises spotted a pod of dolphins. This was a great introduction to Annapolis and the Bay! We both agreed this would be a great place to bring out of town visitors for a unique and fun experience. We will absolutely return again, koozies in hand.

Not a bad sail for two people at $98. It can get a little crowded but people usually tend to all sit together , we opted to sit in the back. There are 2 bathrooms located in the boat. A kind-of tour guide or maybe it was the captain (We couldn't hear anything at back of boat ) . Your trip comes with a snack and soda drink. They provide pretzels, cookies, variety of chips. The crew were a handful of youngsters but were very professional and very kind. Beers were about $6-$8 each but they provide local beers which was cool for the experience. Pretty good tasting as well. We went on a nice and sunny day with good amount of wind. Many people were on the water. It was beautiful !! The crew were so nice and offered to take photos and held good conversation. Only tip for yelpers is to check in before you enter the boat and you need to get a pass for free drink and your free coozie before you leave as the crew doesn't know anything about yelp. Missed out on my free beer because of this (and because my WiFi was not working) Will definitely look to a return trip as they give you a card to log your trips and I believe the 6th one is feee with a t shirt!

I took a Woodwind cruise as part of a lovely bachelorette party, and we loved the stunning views, wine, and educational experience. A one-of-a-kind experience!

Great opportunity to experience sailboat racing with a seasoned Captainand crew. Booking was extremely easy not complex. Recommend going on Wednesdays because that's a local weekly activity. Go no matter the weather. Go CPT Jen!

Awesome end to our vacation in Annapolis. Very friendly captain and crew, we had an amazing time.

Perfect night with the perfect crew! Mickey, Ed and Sophia were so accommodating and knowledgeable. Highly recommend the sunset sail!

Too much talking. If no wind they just motor around Naval Academy. Barely got to mouth of Severn in two hours.

Came here with folks from work (did not drive here). It is located right behind a hotel, which we walked through to get to the boat. The employees on the boat were wonderful from start to finish. Before going on this adventure, my concern was that I needed to have a life vest as I would have never done it. Lo & behold, as soon as I stepped on the boat, I was informed that a life vest was set aside for me. During sailing, the staff of 3 or 4 (can't remember) informed us if we needed anything to let them know and they walked by us periodically to see if we ever needed anything. Some of us participated in putting up the sails and even steering the boat. Whenever we docked, the staff always offered a helping hand to safely get us off the boat. Very pleasant experience, and I am looking forward to doing it again. I parted with a frequent sail card, now if I can just find it in time for next summer.

Sailing with the schooner Woodwinds crew is a tradition for me several times throughout the season, annually. I've come to enjoy bringing family or friends aboard for a day cruise or charter for special occasions. The captains are wonderful, knowledgable and very accommodating; and it is wonderful to be able to share my joy for sailing. This is a great way to see Annapolis and the sights be it team build or enjoy some time with loved ones. Highly recommend!

Captain Jen, Ed, and Andrew made a gray and drizzly trip fun, exciting, and interesting! We loved being on the water, steering the boat, and hearing about local historical facts. We had beautiful sunny weather last year on a sunset cruise with Woodwind and had an equally good time on this one. We will definitely be back!!

Great sail, great crew, fun time tasting Port city beers with the brewery founder. First class operation and they do more sailing than other tourist sails I've been on.

First sail with Schooner Woodwind this weekend, I'll be back many times with friends/family when they're visiting. The craft beer selection on board was impressive. Crew was great!

I have no doubt if you get to go on this excursion it's probably quite lovely based on other reviews. The problem is their cancellation policy is awful which yes they do make well known upfront. (Moral of the story just don't book in advance if at all there are companies locally with more reasonable accommodations if you need to book farther out) It's quite an investment to not even offer a raincheck when the conditions were as poor as ours were and the eye rolls from the staff who were all hiding under cover as they explained they were rain or shine with no rescheduling. Ended up having to cancel another local reservation just so we could go home early. One of the poorer interactions I've had in some time for something that we were looking forward to. Staff made it quite clear we should've looked at the forecast (booked over a week out) which sure is fine. Their crew was quite happy we canceled and they got their money without having to go out because no one wanted to go out in it. Not a great way to run a business. I hope others avoid the same experience and only experience it when they are not in that situation. Between the bad policy (no one asked for a refund just a raincheck) and the smug employees I was happier to walk away. Book at your own risk.

Fantastic day on the water with Captain Jen and her crew! If you are in Annapolis, I highly suggest you take a sail with this team!!

Captain Andy and Crewmembers Ed and Nellie were personable and skillful sailors. Made for an enjoyable afternoon on the Chesapeake Bay.

We had so much fun. It was a gorgeous day and the crew was fantastic. Loved helping to hoist the sail and steer! Free koozy and beer with Yelp check-in was an extra bonus! Looking forward to my next trip

For $50 a pop, you get to ride the same schooner that was featured in Wedding Crashers with Christopher Walken, Vince Vaughn and Owen Wilson. My friend was up visiting me from Nashvegas, and we took a day trip to Annapolis. I really didn't have a set agenda for the visit other than I wanted to take him out on the Bay. How this was going to be accomplished would be figured out once we got to the marina Once we arrived to the Annapolis downtown marina, there apparently was a boat show going on that we were unaware of. We learned of the Schooner Woodwind by the ticketers at the gate of the boat show. 20 minutes left until their final outing for the day, we rushed over to the location where we bought tickets and departed for our quest. We had such a fantastic experience. It wasn't too hot and it wasn't cold. It had a small breeze and cloudy. The weather and the people completely made the 2 hour voyage completely worth the while. We got to take a hold of the boat wheel and guide it with a little help from the captain on board. Since there wasn't but 14 people on the boat versus their sometimes 50 capacity - we really lucked out at having a more personal experience than say if we came on a clear weekend day in June. We came in mid April on a Friday. With your $50 ticket - you get a non-alcoholic beverage and snack through mid trip. Alcohol is available for purchase. Yelp side note - if you check in, they give you a free coozy that gives you a free alcoholic beverage of either wine or beer. Otherwise the coozies are $3 and you buy that from the place you get your ticket on the doc. If you want to bring your family out on the Bay for an afternoon of sailing; this is the best recommendation I can give you. It was totally 10,000% worth the money spent.

Had an amazing time on the Monday history sunset cruise. The crew was amazing and made the experience that much better. Definitely worth the money.

Highly recommended as a relaxing COVID-friendly activity. Every group gets their own section of the boat to enjoy with plenty of space to stretch out. Drink service was great with reasonable prices - we had a couple rounds of tasty bloody marys followed by some great local craft beer. If you're looking to kick back on the open water and enjoy the Annapolis scenery for a couple hours, this should be on your list.

While our day was pretty mild as far as wind, the day was spectacular! The crew did an excellent job of keeping everyone hydrated and the captain and was really knowledgeable (or so it seemed!) of the bay, the area and the job! I would definitely recommend it to anyone!

We had a FABULOUS time on a Sunset Sail with this company. The boat didn't feel overcrowded, and it was the perfect amount of time to be on the boat (about 2 hours). Try to sit near the captain's wheel if you go - our captain gave out really interesting facts about what we were sailing by. They also provide free soft drinks and a little snack. Will definitely take another cruise with them when I have family in town!

If you can do one boat tour while I'm Annapolis, this is the one you have to do! If you can do the sunset tour, I recommend that. I originally went on a 4pm tour. It was amazing! The captain was very entertaining. I heaved the sail up! Volunteer for that if you can! So much fun. That sail was awesome. I loved it so much after graduation from an Army class I was taking at Fort Meade, my two friends and I did the sunset cruise. It was beautiful! Again, captain and crew were awesome. Drinks on board, cash only. But only 7$ a beer. They have a special beer you can only get on the boat or at Hysteria brewing. It was a perfect way to spend 2 hours with friends! I only wish I lived closer, I would do this over and over again. When I visit, I definatley will!

Was a great time! The captain and crew were very attentive and informative. It was not too crowded with covid and I felt safe